WO2012150523A1 - Method for the oriented crystallization of materials - Google Patents
Method for the oriented crystallization of materials Download PDFInfo
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- WO2012150523A1 WO2012150523A1 PCT/IB2012/052026 IB2012052026W WO2012150523A1 WO 2012150523 A1 WO2012150523 A1 WO 2012150523A1 IB 2012052026 W IB2012052026 W IB 2012052026W WO 2012150523 A1 WO2012150523 A1 WO 2012150523A1
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- WIPO (PCT)
- Prior art keywords
- particle
- crystallized
- group
- interest
- functionalized
- Prior art date
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02296—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer
- H01L21/02318—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment
- H01L21/02356—Forming insulating materials on a substrate characterised by the treatment performed before or after the formation of the layer post-treatment treatment to change the morphology of the insulating layer, e.g. transformation of an amorphous layer into a crystalline layer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/191—Deposition of organic active material characterised by provisions for the orientation or alignment of the layer to be deposited
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having a potential-jump barrier or a surface barrier
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
Definitions
- the present invention relates to the field of crystallization of materials and aims in particular to provide a method useful for controlling and orienting the formation of a crystalline deposit of a material on the surface of a substrate.
- It also relates to devices, for example electronic or optoelectronic devices, comprising a crystallized material, in particular in the form of a thin film, obtained according to such a method.
- Organic semiconductors are currently experiencing considerable growth in the world of electronics and information technology. They can indeed be substituted for silicon in the manufacture of electronic or optoelectronic devices such as organic electroluminescent devices, organic photovoltaic devices and organic transistors.
- crystals in particular in the form of thin films, from organic or inorganic materials, in which the crystallization is homogeneous, and preferably controlled.
- the first is to heat the substrate, generally prior to the deposition step of the organic semiconductor, to promote an organized growth of organic semiconductor crystals.
- the second is to design new organic semiconductor molecules from already known molecules, so as to provide these new organic semiconductor molecules with better crystallizability.
- document US 2007/0243658 describes a process for manufacturing a thin film of organic semiconductors crystallized on a substrate comprising a first step of coating said substrate with a solution of said organic semiconductor followed by a step of crystallizing said organic semiconductor initiated from the end of said coating.
- the present invention aims precisely to provide a new method useful for orienting the crystallization of a material on the surface of at least one face of a substrate.
- the present invention relates, according to a first of its aspects, a method useful for orienting the crystallization of a material on a surface area of at least one face of a substrate, comprising at least the steps of:
- contacting said particle with at least said material to be crystallized iv. exposing at least said point of contact between said particle and said material to be crystallized at conditions favorable to the crystallization of said material, said method being characterized in that the surface of said particle is partially functionalized by at least one group said to have affinity for said material to be crystallized, said group having at least one pattern of identical or similar chemical nature to at least a part of the chemical structure of said material to be crystallized, and in that said particle is deposited in step ii. in order to expose said group facing the area of interest.
- the inventors have found that it is possible to orient the crystallization by means of a functionalized particle deposited on the surface on which the crystalline deposit must be formed.
- the partially functionalized molecule will make it possible to initiate and orient the germination and / or the growth of the material to be crystallized, in a localized, oriented and organized manner in the direction of the functionalized part. of the surface of the particle.
- the crystallized material obtained by the process according to the invention is homogeneous, organized with a very large order factor and oriented on the zone of interest.
- this crystalline deposit may even consist of a single monocrystalline grain of the material in question.
- the method according to the invention makes it possible to obtain a crystalline deposit of very good quality, exhibiting very good mobility of the charge carriers, and therefore electrical properties. very satisfying, in the area of interest.
- the method according to the invention has the advantage of being easy to implement, insofar as it is compatible with the implementation of conventional deposition or printing techniques, and thus be inexpensive. .
- the invention also relates, in another of its aspects, a device, for example photovoltaic or photoconductive, comprising a crystalline deposit, in particular in the form of a thin film, obtained by the method according to the invention. It is advantageously transistors, including field effect and diodes. Other characteristics, variants and advantages of the method according to the invention will emerge more clearly on reading the description, the examples and figures which will follow, given by way of illustration and not limitation.
- the method according to the invention involves, in a first step, determining on the face of the substrate considered a particular surface area corresponding to the surface on which the crystalline deposit of the material in question is intended to be formed.
- substrate refers to a basic structure on the surface of which is formed the crystalline deposit of the material in question according to the invention.
- the method according to the invention can advantageously be implemented on various substrates.
- This substrate can therefore be very diverse in nature, organic or inorganic, or even composite in nature, that is to say formed of several different materials.
- the substrate can thus be based on silicon, glass, a metal and / or a resin and generally be in the form of a plate, a sheet or a film. It will be more particularly a substrate based on resin.
- silica silicon, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyimide (PI), polyetherimide ( PEI), polyether sulphone (PES), polysulfone (PSF), polyphenylene sulphide (PPS), polyether ether ketone (PEEK), polyacrylate (PA), polyamide imide (PAI), polystyrene, polyethylene , the polypropylene, a polyamine resin, a carbonate resin or a cellulosic resin.
- It may in particular be a composite material formed by conductive zones, in particular metal zones, juxtaposed with insulating zones.
- the substrate may, if appropriate, undergo prior to its treatment according to the invention, one to several transformations dedicated for example to confer special specificities such as for example a functionalization with one or more ancillary materials, such as for example metals to form one or more electrodes.
- one or more ancillary materials such as for example metals to form one or more electrodes.
- the process according to the present invention proves particularly advantageous for forming thin films, for example of organic semiconductors, required in the field of electronics and in particular transistors, as illustrated in the example which follows.
- Area of interest for example of organic semiconductors, required in the field of electronics and in particular transistors, as illustrated in the example which follows.
- the surface area on which the crystalline deposit is to be formed is called "area of interest" in the context of the present invention.
- crystalline defect is meant in particular to designate the interfaces between two crystals in a polycrystalline structure (also called grain boundaries).
- zone of interest within the meaning of the invention can thus be defined as being the surface where the crystalline deposit must be as uniform as possible, or even consist of a single monocrystalline grain.
- the "area of interest" within the meaning of the invention is the area within which a stream of electrons or holes must be transported.
- the "zone of interest” in the sense of the invention associated with a material of crystallization of organic semiconductor type is the zone of the channel between the source and drain electrodes .
- zones of interest within the meaning of the invention are in particular in the diodes, the capacitors, in particular the MIS (metal / insulator / semiconductor) capacitors, or the optical detectors.
- the method according to the invention comprises at least a second step (ii) of depositing on said face and at the periphery of said zone of interest, at least one particle dedicated to form a crystallization seed.
- the particle dedicated to forming a crystallization seed has part of its surface functionalized by at least one affinity group for said material to be crystallized.
- It may have a size ranging from 10 nm to 100 ⁇ , or even greater than 100 ⁇ .
- the size of the particle can be adapted to the size of the area of interest to ensure the best crystallization in this area.
- the particle may have a dimension close to the dimension of the side of the zone of interest where it will be positioned: the crystallization will spread homogeneously over the entire surface.
- Its shape can also be adapted: for example, an elongated shape for a zone of interest in the form of a parallelogram.
- the particles can be distributed along one of the sides of the zone of interest to homogenize also the growth front.
- It may be a particle selected from semiconductor particles such as particles of Si, Ge or pentacene; the insulating particles such as silica particles, polystyrene, or Teflon ®; conductive particles such as particles of Ni, PDOT (poly (3,4-ethylenedioxythiophene)) or ITO (indium tin oxide), and ceramic particles such as particles of barium titanate BaTiO 3 .
- semiconductor particles such as particles of Si, Ge or pentacene
- the insulating particles such as silica particles, polystyrene, or Teflon ®
- conductive particles such as particles of Ni, PDOT (poly (3,4-ethylenedioxythiophene)) or ITO (indium tin oxide)
- ceramic particles such as particles of barium titanate BaTiO 3 .
- said particle is inorganic.
- it may be formed entirely or partly of oxide, advantageously silica, alumina, barium titanate (BaTiO 3 ).
- the particle is a silica particle.
- the particle is functionalized on a part of its surface by an affinity group for the material to be crystallized.
- affinity group for said material to be crystallized is intended to mean a group having at least one chemical unit identical or related to at least a part of the chemical structure of said material. to crystallize.
- said functionalization group may advantageously have an aromatic unit, in particular phenyl.
- a partially functionalized particle according to the invention may be prepared according to functionalization techniques known to those skilled in the art.
- Functionalization by said specific group described above can thus be performed by grafting onto said portion of the surface of the particle, a molecule comprising said chemical pattern considered to constitute a self-assembled monolayer, also called SAM (in English: Self-Assembled Monolayer ").
- SAM self-assembled monolayer
- the SAM molecule has in particular, in addition to the specific group, at least one so-called reactive function capable of allowing its grafting on the surface of the particle.
- the chemical unit of the group considered according to the invention is totally inert with respect to the surface of said particle to be functionalized.
- inert still indifferently said “non-reactive” means that said pattern does not react or does not interact or induces any action with the surface to be functionalized.
- the particle After grafting the SAM, the particle has a portion of its surface functionalized by said groups having the specific chemical pattern.
- the functionalization of the considered surface of the particle can be carried out directly, for example by a vacuum treatment, by depositing a SAM on the part of the surface to be functionalized.
- the particles may thus already have a surface comprising functions capable of interacting with said reactive function of the carrier molecule of said group considered, to allow its grafting.
- the functionalization of a portion of the surface of the particle may require prior treatment of said surface portion of the particle in order to generate functions capable of interacting with said reactive function of the SAM to allow its grafting.
- the interaction of the reactive function of said SAM and the function generated on said surface of the particle allows the establishment of a covalent link between said functions.
- the particle to be functionalized (1) for example a silica particle
- Functionalization of said surface by said groups is then ensured by bringing said surface into contact with a molecule carrying said group having said affinity unit for the material to be crystallized, for example a phenyl radical for aromatic materials, and a function reactive capable of interacting with a hydroxyl function of the surface to form a covalent bond.
- a molecule carrying said group having said affinity unit for the material to be crystallized for example a phenyl radical for aromatic materials, and a function reactive capable of interacting with a hydroxyl function of the surface to form a covalent bond.
- the particle having on one part of its surface hydroxyl functions is for example immersed in a solution comprising the SAM molecule.
- the molecule of the SAM (4) may for example carry, in addition to the particular phenyl aromatic unit of interest, at least one silane or chlorine or isocyanate functional group, capable of interacting with a hydroxyl function of the surface by silanation reaction, chloride- silica or isocyanate-silica, to form a covalent bond.
- Such a molecule may be in particular phenytriisopropylsilane or phenyltrimethoxy silane, preferably phenyltriisopropylsilane.
- the final particle (5) obtained is functionalized, on the part of its surface previously carrying hydroxyl functions, with groups having a phenyl unit (6).
- the particle is bifunctionalized.
- bifunctionalized is meant that two distinct parts of the surface of the particle are functionalized by distinct groups.
- said particle may be functionalized on another part of its surface by a group devoid of affinity for said material to be crystallized.
- said affinity groups for the material to be crystallized and said groups devoid of affinity for said material to be crystallized are arranged on different faces, preferably opposite to said particle.
- the particle has two very different faces, one face that will have an affinity with said material to be crystallized and another face that will strongly push said material to be crystallized.
- Said groups devoid of affinity for the material to be crystallized are such that no crystallization can be initiated during the bringing into contact of said material to be crystallized and the part of the surface of the particle functionalized by said group lacking affinity for the material to crystallize.
- the bifunctionalization of the particle may, for example, be carried out via two consecutive plasma treatment steps, as described more particularly below.
- said group lacking affinity may be a fluorine atom or an amine, in particular a fluorine atom.
- the particle previously functionalized on part of its surface by hydroxyl functions may, prior to its introduction into the solution comprising the molecule SAM, be exposed to a fluorinated plasma, so as to functionalize the part of its surface containing no hydroxyl functions by fluorine atoms.
- the particle obtained is thus functionalized on one of its faces by hydroxyl functions and on the other side by fluorine atoms.
- the particle is then immersed in a solution comprising the silane-derived molecule, in particular phenytriisopropylsilane or phenyltrimethoxysilane.
- Fluorine the difference in hydroxyl functions, is not able to interact with a silane function of the molecule used. Therefore, the molecule can be grafted only on the part of the surface of the molecule containing hydroxyl functions.
- the final particle has part of its functionalized surface with groups having a phenyl unit and another part of its surface containing fluorine atoms. Deposition of said particle
- the particle is deposited according to step (ii) on said face so as to expose said affinity group for the material to be crystallized, facing the area of interest.
- said particle is deposited outside the zone of interest, more particularly at the periphery of the zone of interest.
- the particle may be deposited in the desired orientation in step (ii) at the surface of said face by various methods, in particular by screen printing, inkjet, buffer or vacuum deposition.
- a buffer in particular an elastomer buffer, and more particularly polydimethylsiloxane (PDMSD).
- PDMSD polydimethylsiloxane
- FIG. 2 schematizes the transfer of the partially functionalized particle (5) by means of a PDMS buffer (6) and its deposition on one of the source or drain electrodes (7) of a transistor.
- the method of the invention also comprises a third step (iii) of bringing said particle into contact with at least said material to be crystallized.
- the materials considered in the context of the invention may be organic or inorganic materials having a high added value in the field of electronics when they are in a crystallized form. It may in particular be organic or inorganic materials with insulating or conductive properties in the crystallized state.
- organic dielectrics in particular polystyrene
- inorganic alloys in particular alloys of the In Cu Ga Se type used in photovoltaic devices
- semiconductors organic compounds, especially as described below.
- these materials are able to crystallize from a liquid solution.
- the material considered according to the invention is an organic semiconductor.
- organic semiconductors considered in the context of the present invention can be of two types.
- They may be low molecular weight molecules (commonly referred to as
- Small molecules and especially molecules with a molecular weight of less than 1000 g / mol, or polymers consisting of macro molecules of greater molecular weight.
- organic semiconductor of low molecular weight there may be mentioned, for example, those of the polyacene, oligo-thiophene or phthalocyanine type.
- organic polymer semiconductors examples include those of polyacetylene, polyphenylene, polythiophene or poly (phenylene / vinylene) type.
- It may especially be an organic semiconductor selected from one of pentacene, tetracene, anthracene, naphthalene, alpha-6-thiophene, alpha-4-thiophene, perylene and its derivatives, rubrene and its derivatives, coronene and its derivatives, perylene tetracarboxylic diimide and its derivatives, perylene tetracarboxylic dianhydride and its derivatives, polythiophene and its derivatives, polyparaphenylene-vinylene and its derivatives, polyparaphenylene and its derivatives, polyfluorene and its derivatives, polyfluorene-oligothiophene copolymer and its derivatives, polythiophene-vinylene and its derivatives, a heterocyclic aromatic copolymer of polythiophene and its derivatives, oligonaphthalene and its derivatives, alpha-5-thiophene oligothiophene and its derivatives, phthalo
- the organic semiconductor is selected from pentacene, tetracene and anthracene. It will preferably be pentacene.
- step (iii) is carried out by deposition on the zone of interest of a continuous film of a solvent medium comprising at least the material to be crystallized according to the invention, said film coming from in contact with said particle.
- the method according to the invention may thus comprise a step of formulating said material to crystallize in the solute state in the solvent medium.
- the deposited film may have a thickness less than or equal to 1 mm, preferably less than or equal to 200 ⁇ .
- This film is more particularly continuous, that is to say that the same uninterrupted film is deposited on the area of interest and at least until contact with said particle.
- Such a continuous film can be obtained by any deposition technique known to those skilled in the art to form thin films on a support.
- the film may be deposited by stamping, spin coating, gravure printing, flexography, inkjet printing, offset, or screen printing.
- the material to be crystallized, present as a solute in the solvent medium must be present in a concentration lower than its critical supersaturation concentration.
- critical supersaturation concentration is intended to mean the limit between the solute state and the solid state, that is to say the stage at which the material passes the solute equilibrium. / solvent medium for precipitating.
- step (iii) of said material to be crystallized with said particle deposited in step (ii) can be carried out by other techniques known to those skilled in the art, such as for example by vacuum deposition or deposition. Physical vapor phase.
- the method according to the invention finally comprises a fourth step (iv) of exposing said point of contact between said particle and said material to be crystallized at favorable conditions for the crystallization of said material.
- step (iv) can in particular comprise at least the evaporation of the solvent medium.
- the crystallization is initiated in a localized manner from the particle deposited in step (ii).
- the crystallization progresses from said particle in an organized manner and oriented in the direction determined by the portion of the surface of the particle functionalized by said affinity group for the material to be crystallized.
- the oriented crystalline deposit obtained is homogeneous in the only direction determined by said surface, with a very large crystallographic order factor, preferably consisting of a single monocrystalline grain of the material to be crystallized.
- FIG. 3 schematizes the continuous film (8) of a solvent medium comprising said material to be crystallized, deposited on the zone of interest and coming into contact with said particle (5).
- the crystallization is initiated from said particle and progresses, simultaneously with the evaporation of the solvent medium, homogeneously in the direction (I) determined by the face of the surface of the particle functionalized by said affinity group for the material to crystallize (5).
- the process according to the invention is particularly advantageous for forming thin films, for example organic semiconductors required in the field of electronics, and in particular transistors.
- the material to be crystallized may be an organic semiconductor.
- Said zone of interest may then be the zone of the channel of a transistor and the particle may be deposited on or at the periphery of at least one of the electrodes of said transistor, said affinity group for the material to be crystallized being exposed facing the canal area.
- the formed crystal will extend into the channel area, preferably in the form of a single monocrystalline grain.
- the method according to the invention can also be implemented with regard to any device requiring the presence of a thin film of a material of very good crystalline quality, such as for example diodes, MIS and detectors.
- the device may be a diode, the material to be crystallized being a semiconductor and the zone of interest being located between the two electrodes.
- said zone of interest is the active zone of a diode and said particle is deposited on or at the periphery of at least one of the electrodes of the diode, said affinity group for the material to be crystallized being exposed facing the active area.
- the material to be crystallized then being an insulator and the area of interest being located between the two frames of the capacitance.
- said material to be crystallized is an insulator, for example polystyrene.
- Said area of interest can then be the gate oxide of a transistor or the dielectric of a capacitance and said particle is deposited at the periphery of the electrodes.
- FIGS. 1, 2 and 3 The exemplary embodiments indicated below or represented in FIGS. 1, 2 and 3 are only given by way of illustration and not limitation of the invention.
- Figure 1 Schematic representation of the functionalization of a portion of the surface of a particle by a group carrying a phenyl unit.
- Figure 2 Schematic representation of the deposition of the functionalized particle using a PDMS buffer on one of the source or drain electrodes of a transistor.
- Figure 3 Schematic representation of the deposition of a continuous film of the solvent medium comprising said material to be crystallized.
- a transistor having the following characteristics has been prepared by implementing the method according to the invention.
- a silica nanoparticle (SiO 2 ) was functionalized on one of its faces by a group having a phenyl unit according to the following method.
- the silica nanoparticle has undergone plasma treatment within an oxygen plasma chamber. This plasma treatment makes it possible to create pendant functions OH " on the part of the surface of the particle facing the plasma.
- the particle is then dipped into a solution of phenyltriisopropylsilane molecule.
- the interaction of silane functions of molecules with hydroxyl functions leads to the grafting of molecules on the part of the surface previously functionalized by the hydroxyl functions.
- the particle obtained has part of its surface functionalized with groups having a phenyl unit. Deposition of the particle
- the particle obtained at the end of the preceding step was deposited on the surface of one of the source or drain electrodes of the transistor, using a PDMS (polydimethylsiloxane) buffer, the treated surface of the nanoparticle by said phenyl groups being oriented towards the conduction channel.
- PDMS polydimethylsiloxane
- the semiconductor liquid pentacene was deposited as a film on the entire plate.
- the solvent medium was then evaporated at 60 ° C for 3 minutes and then at 100 ° C for 1 minute.
- the crystallization is initiated in contact with the particle. It is oriented and organized according to the direction of the face of the particle functionalized by the groups carrying phenyl units. Deposition of the gate dielectric and the conductive grid
- the dielectric polystyrene
- the Ag ink jet deposit was deposited by screen printing, and then by the Ag ink jet deposit to form the gate of the transistor.
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12720647.2A EP2705551B1 (en) | 2011-05-04 | 2012-04-23 | Method for the oriented crystallization of materials |
KR1020137032224A KR20140027391A (en) | 2011-05-04 | 2012-04-23 | Method for the oriented crystallization of materials |
JP2014508895A JP2014518013A (en) | 2011-05-04 | 2012-04-23 | Oriented crystallization method for various materials |
CN201280032942.7A CN103650188A (en) | 2011-05-04 | 2012-04-23 | Method for the oriented crystallization of materials |
US14/115,613 US9548454B2 (en) | 2011-05-04 | 2012-04-23 | Method for the oriented crystallization of materials using a particle as a crystallization nucleus that has a surface partly functionalized with at least one group having an affinity for the material to be crystallized |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1153836 | 2011-05-04 | ||
FR1153836A FR2974945B1 (en) | 2011-05-04 | 2011-05-04 | PROCESS FOR ORIENTED CRYSTALLIZATION OF MATERIALS |
Publications (1)
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WO2012150523A1 true WO2012150523A1 (en) | 2012-11-08 |
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PCT/IB2012/052026 WO2012150523A1 (en) | 2011-05-04 | 2012-04-23 | Method for the oriented crystallization of materials |
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US (1) | US9548454B2 (en) |
EP (1) | EP2705551B1 (en) |
JP (1) | JP2014518013A (en) |
KR (1) | KR20140027391A (en) |
CN (1) | CN103650188A (en) |
FR (1) | FR2974945B1 (en) |
WO (1) | WO2012150523A1 (en) |
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CN107925000A (en) * | 2015-08-06 | 2018-04-17 | 默克专利股份有限公司 | Organic semiconductor composition and its purposes in manufacture organic electronic device |
WO2017159025A1 (en) * | 2016-03-15 | 2017-09-21 | ソニー株式会社 | Photoelectric conversion element and solid state image pick-up device |
CN107523290B (en) * | 2016-06-20 | 2019-10-18 | 国家纳米科学中心 | One organic molecular species two dimensional structure and preparation method thereof |
US20220045274A1 (en) * | 2020-08-06 | 2022-02-10 | Facebook Technologies Llc | Ofets having organic semiconductor layer with high carrier mobility and in situ isolation |
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US20070243658A1 (en) | 2006-04-14 | 2007-10-18 | Katsura Hirai | Production method of crystalline organic semiconductor thin film, organic semiconductor thin film, electronic device, and thin film transistor |
US20070252229A1 (en) * | 2006-04-26 | 2007-11-01 | Masaaki Fujimori | Field Effect Transistor and Manufacturing Method Thereof |
US20090101893A1 (en) | 2007-06-22 | 2009-04-23 | Cambridge Display Technology Limited | Organic Thin Film Transistors |
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JP4736340B2 (en) * | 2004-03-31 | 2011-07-27 | 大日本印刷株式会社 | Organic semiconductor structure, manufacturing method thereof, and organic semiconductor device |
JP4847050B2 (en) * | 2004-06-07 | 2011-12-28 | 扶桑化学工業株式会社 | Film forming composition and film forming method |
JP4996846B2 (en) * | 2005-11-22 | 2012-08-08 | 株式会社日立製作所 | Field effect transistor and manufacturing method thereof |
JP2007173728A (en) * | 2005-12-26 | 2007-07-05 | Seiko Epson Corp | Method of manufacturing organic ferroelectric capacitor, organic ferroelectric capacitor, organic ferroelectric memory, and electronic apparatus |
US7795145B2 (en) * | 2006-02-15 | 2010-09-14 | Basf Aktiengesellschaft | Patterning crystalline compounds on surfaces |
JP5103957B2 (en) * | 2007-03-13 | 2012-12-19 | コニカミノルタホールディングス株式会社 | Thin film crystal manufacturing method, organic thin film transistor manufacturing method |
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2011
- 2011-05-04 FR FR1153836A patent/FR2974945B1/en not_active Expired - Fee Related
-
2012
- 2012-04-23 KR KR1020137032224A patent/KR20140027391A/en not_active Application Discontinuation
- 2012-04-23 CN CN201280032942.7A patent/CN103650188A/en active Pending
- 2012-04-23 EP EP12720647.2A patent/EP2705551B1/en not_active Not-in-force
- 2012-04-23 WO PCT/IB2012/052026 patent/WO2012150523A1/en active Application Filing
- 2012-04-23 US US14/115,613 patent/US9548454B2/en active Active
- 2012-04-23 JP JP2014508895A patent/JP2014518013A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US20070243658A1 (en) | 2006-04-14 | 2007-10-18 | Katsura Hirai | Production method of crystalline organic semiconductor thin film, organic semiconductor thin film, electronic device, and thin film transistor |
US20070252229A1 (en) * | 2006-04-26 | 2007-11-01 | Masaaki Fujimori | Field Effect Transistor and Manufacturing Method Thereof |
US20090101893A1 (en) | 2007-06-22 | 2009-04-23 | Cambridge Display Technology Limited | Organic Thin Film Transistors |
Also Published As
Publication number | Publication date |
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JP2014518013A (en) | 2014-07-24 |
KR20140027391A (en) | 2014-03-06 |
CN103650188A (en) | 2014-03-19 |
EP2705551A1 (en) | 2014-03-12 |
US20140127855A1 (en) | 2014-05-08 |
FR2974945A1 (en) | 2012-11-09 |
FR2974945B1 (en) | 2013-06-28 |
US9548454B2 (en) | 2017-01-17 |
EP2705551B1 (en) | 2015-01-14 |
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